


Mandy

by belovedhell



Category: Supernatural
Genre: Assault, Bottom Sam, Crossdressing, Dorks in Love, False Identity, First Time, Fluff, Light Angst, M/M, Protective Dean Winchester, Sibling Incest, Weecest, homophobia mention
Language: English
Status: Completed
Published: 2016-12-19
Updated: 2016-12-19
Packaged: 2018-09-09 18:34:11
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 1
Words: 4,477
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8907418
Author URL: https://archiveofourown.org/users/belovedhell/pseuds/belovedhell
Summary: Sam dressed up as a girl in order to go out with Dean. Good Plan? Yes. Backfired? Definitely. Getting assaulted, missing their date, and lastly, Dean finding him both hurt and in a dress was not good. But it would appear that Sam wasn't the only one holding a big secret.





	

**Author's Note:**

> One story down. Two more wincest stories to go. I finished this fic few days ago but finally got to upload it today. Busy weekend. Comment and Kudos are lovely and appreciated. Also, did this fic for clearlylostmymind from tumblr. Couldn't help myself!

Sam let out a shaky sigh as he finished putting eyeliner on. He put on some blush, red lipstick, and smokey eye shadow. He looked stunning, he appeared like a delicate girl. Dean would love this for sure.

John found a hunt in a small town; people were disappearing and only their hearts would be found. Therefore, John was stuck in the same area until they found the son of a bitch that was doing the gruesome killings. So far he had found no traces of the monster, even after three months had passed. The mission seemed too dangerous for his boys so he told them to stay put in a small apartment for the time being.

Being in an apartment alone with Dean was nerve racking, Sam would fidget and babble nonstop about random things. Sam had been in love with Dean for a long time. The way Dean would smile lovingly and ruffle his hair with a grin. How could he not fall in love with his older brother?

The first few weeks were awkward, but then it got somewhat normal after Sam had stopped blushing like an idiot. And then there were times when Dean would go out to a bar... leaving Sam all by himself. Sure, Sam was a big boy— sixteen— but still. It hurt. A lot. It broke Sam's heart when he would see Dean coming back with a few hickeys on his neck.

Thus, one day Sam got a stupid idea. What if he dressed up like a girl and made Dean fall in love with him? The idea wasn't that bad. It worked. Dean had no clue it was Sam who wore dresses and makeup on their dates. In fact, Dean was being fooled. Sam felt bad but it was his only opportunity to be with Dean. A little desperate? Yes.

Which brought him back to his current situation— He was meeting Dean in a nice restaurant in half an hour. Their seven date. Dean was a gentleman and just amazing. Sam could compliment him all he wanted and he could kiss Dean without freaking out. Why didn't he think of this sooner?

Glancing at himself in the mirror, Sam smiled in satisfaction. He straightened his medium-length, brown hair; having shaggy hair wasn't very appealing for a girl— according to teen magazines. Then on clothing Sam was wearing a wool, white unbuttoned sweater and underneath revealed a teal dress that reached his knees. He wasn't Sam anymore, he was Mandy now. What? He needed a fake girl name to fit his new identity for the time being.

Blushing embarrassingly, Sam thought of Dean's grin every time he dressed up.

"Go get him tiger," Sam told himself. Taking one final look at his refection, he left the bathroom. Dean wasn't home. Thank god. He had a habit staying late at the auto mechanic shop where he worked. Sam told— well, lied— to Dean, he said he would be in the library all day working on homework.

A perfect excuse.

While everything was going great between them. Dean had been getting a little handsy lately. Slipping his hand underneath his shirt and would sometimes pull the hem of his skirt. Sam had to swat his hands away before things got sexual— also so he wouldn't notice that he had a dick and no titties.

Dean would probably punch him, whether or not he knew it was Sam. Dean hated when someone would lie to him. It would hurt more that it was his little brother.

Sam— No, Mandy, would meet Dean in the same diner right beside the auto shop. Sam had no phone unlike Dean, therefore communication was difficult for them. He had to come up with an excuse as to why he didn't have a phone. Mandy's excuse was that her father was very strict and didn't allow technology in the house. Luckily, Dean bought it.

They met earlier in the diner to discuss about their date. Dean suggested a fancy date in a well-known restaurant in town. Sam was thrilled. Both agreed to meet up at seven. It gave Sam enough time to get ready and prepare himself.

As he began to walk out of the apartment, he heard a familiar rumble approaching— Shit! It was the Impala... Dean was home early. Sam turned both ways to see if there was some place he could hide. The Impala could be heard coming closer.

Sam had no choice but to hide behind some bushes near the building. He wondered why Dean was home? Then again, he still had twenty minutes to spare. Maybe, he forgot something.

Sam sighed in relief. Happy that he got out before Dean had a chance to see him. It could have been a disaster. Dean would probably never talk to him again—or worse— say he was sick in the head. Sam didn't want that to happen. He just wanted to have Dean... he just wanted to have a small taste of his desire.

"Better get going." Sam took the opportunity to get away. He took a shortcut so his brother wouldn't see him walking on the sidewalk. It would be weird if Mandy was walking near the apartment where Dean lived, not to mention suspicious.

The sun was starting to set, Sam had to hurry up before it got dark. He didn't want to be late for his date. Sam's heart would melt at the sight of Dean waiting for him— erm — Mandy.

He made sharp turns through a few blocks, careful to avoid being seen. He entered in a filthy ally. It sent a shiver down Sam's spine as he saw caught a whiff of what appeared to be death. He quickly paced ahead. Suddenly he halted as he saw a glimpse of older guys at the end of the ally.

Usually Sam wouldn't care, but he was dressed up as a girl, therefore it was not going to end well. Damn it. He had to cross this path in order to get to the restaurant faster. He couldn't go to another way... otherwise he would miss his date.

Debating, Sam decided to go straight. He was not going to disappoint Dean. He worked so damn hard to look good.

As he passed them, Sam didn't make any eye contact as he rushed his pace. Sam was almost there. From behind he could hear footsteps coming closer and few shadows appearing near him. Sam gulped.

"Are you lost, sweety?" a low voice from behind said.

"No," Sam uttered out. "I'm on my way to see my _boyfriend_." Laughter could be heard, causing Sam to shake in fear. There were three of them and he was outnumbered.

"All alone out here? Some boyfriend." The shady guy stood right beside Sam, "I can show you a _real_ good time."

When an arm made its way around Sam's waist, he flipped. "Get away from me! I'm not interested—" Sam winced when the guy yanked his hair.

"Aren't you a bitch? And here I was trying to play nice. We could do this the hard way." His face was so close to Sam that it made him gag.

"Fuck off!" Sam elbowed the guy in the face, once he was free he tried to run. He had to get away quick. Abruptly, he was pushed against the wall and to make it worse his cheek connected— and scraped— to the bricks.

"You bitch! You're going to pay for that." Sam's eyes widened as he felt his clothes being ripped apart. He thrashed like a maniac and then pushed himself off the wall with incredible strength.

Sam threw a couple of punches to the guys, easily dodging theirs. One managed to get an upper hand and hit a direct punch onto his abdomen. As Sam slightly bent down, the main leader took the opportunity to slap him, hard. Oh, what a gentleman?

The top part of his dress ripped, revealing his chest... and real gender.

"You're a guy?!" they all said in disgust. Sam growled in anger, they ruined his outfit that he worked so hard to find. He popped his knuckles and made sure every guy collided with the wall. He heard the leader say the word faggot, which earned him a kick in the face. For good measure.

Sam was pissed off, but it faded as he looked at the sky. It was dark around and he could see a hint of stars appearing. The lamppost's lights were on already, he hadn't realized it.

He didn't know if he missed his date, yet there was no way he was going now. All his hard work was ruined. His dress was tore and his makeup was smeared. Sam felt pain on his face... it was most likely bruised and bleeding from the cuts he received. Sam frowned. He had to go home and change.

Sam went the same way he came from. He was heartbroken. He was looking forward to chatting and kissing Dean, having his strong arms holding him as they gazed at the stars.

Fuck. How was Sam going to do it now? With his injured face, Mandy couldn't see Dean, not without figuring out that they both have the same wound in the same spot. Dean would automatically catch on. Sam was screwed. Well, this was the end of Mandy.

At least Sam got to be with Dean just a little. That was more than enough. More than he hoped for.

As he entered inside the empty apartment, Sam felt horrible that Dean was waiting for him in the restaurant. Sighing, he grabbed his duffle bag and made his way to the bathroom. His eyes lowered as he saw his reflection; his cheek was fucking bleeding. Multiple cuts were across his cheek to chin. Sam needed to wash the makeup off before it got infected.

Turning on the sink, he splashed his face with cold water. It stung a little. He watched the water turned into a mess of colors as the makeup came off. Sam opened his duffle bag and pulled out a set of clothes and a towel. A knock startled him.

"Sam?" Dean said from the other side. What the fuck time was it?

"Y-Yeah? Dean? You're home early," Sam tried to keep his voice steady as he possibly could. He was glad he locked the door.

"My date stood me up..." Dean said. "I was waiting there like a dumbass for twenty-five minutes." Twenty-five minutes? Sam felt even guiltier.

"I'm sorry. You should call her," Sam suggested, playing dumb.

Dean snorted, "No phone remember." Then his tone went softer, "I-I don't understand. Mandy never forgot any of our dates. Why do you think that is, Sammy?"

Sam shut his eyes, Dean was hurt. That was something he never intended to do. "Maybe you should forget about her." Sam stared at himself in the mirror and continued, "You could do better anyway." He spoke truthfully. Dean deserved a girl who would make him happy every day.

He heard Dean cussed and tried to open the door. "Why the fuck do you have the door lock? Open the door, Sam!" Okay, now he seemed pissed.

"I'm busy!" Sam countered, quickly wiping his face with the towel— accidentally rubbing on his wound. "Fuck!" Sam cried out in pain. He held his injured cheek gently as his eyes got watery.

"Sam? Sam!" Dean panicked. Then without thinking he kicked the door open and bolted inside, expecting something to be hurting Sam. But Dean stopped dead in his tracks at the sight of seeing Sam injured— Now that was something he wasn't expecting to see.

Sam froze on the spot as Dean burst inside. Oh no... He hadn't changed yet and the makeup wasn't completely off. "Dean, get out of here," it didn't come out confident, rather scared.

He expected Dean to shout at him, or at least make a disgusted expression.

However, he didn't do either or, instead he rushed to Sam's side and grabbed his chin as he turned it. "Who did this to you?" Dean growled. "Who the fuck hurt you—" Dean's mouth opened and his expression morphed into horror when he saw Sam's ruined outfit. "Did they..." he left the sentence hanging for Sam to finish it, praying to god that it wasn't...

"What— No, No! They didn't do anything," he assured, putting his hand on top of Dean's. "I'm fine, Dean." Sam was grateful when Dean didn't question his girly clothing. Leave it to his brother to be more worried about his injuries than his ridiculous outfit.

Dean seemed to calm down, slightly, although he raised his voice in a big brother tone. "Like the hell you are? Look at your face. I'll kill them, whoever touched you. Damn it… I should've been there." Dean's eyes slanted as he let go of Sam. "I knew something was wrong the minute you didn't show up," he muttered the last part to himself.

Sam didn't catch what Dean said in the end. "It's fine. I was outnumbered but I still kicked their asses. Don't worry, Dean." He put a smile on for his sake. Sam hated when Dean would guilt himself every time he got hurt. It wasn't his fault.

"There were more?" Dean's eyes widened in shock, then his anger returned. "Son of a bitch! I'm going to fucking find them and—"

"Dean!" Sam grabbed his face with both his hands, causing his brother to stop spouting nonsense and having his full attention. Both locked gaze as Sam said, "I'm fine. Nothing happened to me. Just a few bruises and scratches, okay? This is nothing compare to the hunts we do."

Dean stilled, and then he softly sighed while Sam was still holding him. "Okay. I'm sorry. I was just worried— Damn, Sam. You're so badly hurt. Let me fix you at least," he offered. Sam hesitated, but seeing Dean with a concerned expression he had no choice but to oblige.

Letting go of him, Sam sat on the edge of the bathtub and averted his gaze elsewhere. Sam didn't have the courage to look at Dean.

"Hold on." Dean left the room momentarily, when he came back he was holding a first aid kit.

Sam glanced at him, finally looking at his older brother— and what he was wearing. He was wearing his favorite Zeppelin shirt and dark blue jeans that weren't too baggy like the others he had. Dean dressed nicely for their date. Sam lowered his head in shame.

"Hey? Sammy, what's wrong?" Dean sat beside him as he opened the kit. "Does it hurt? Are you in pain?"

Shaking his head, Sam replied with something else, "Your girlfriend was stupid to miss your date."

"Quit talking like that," Dean huffed. "Maybe Mandy had a good excuse for missing our date."

Sam didn't reply, instead his shoulders slouched in defeat. Dean was always a good guy, he never liked when Sam would talk badly about _Mandy_. In fact, he always defended her… Dean really liked her. Sam recalled all the times Dean would brag about Mandy and how amazing she was. Sometimes Sam couldn't help but badmouth her— it was stupid and immature and ironic because it was himself. Yet, it didn't stop Sam from envying Mandy one bit.

Dean began to clean his wound, gently, and wiped away any bit of dirt and gravel he had that stuck between his inner skin. Sam bit his lips, trying to suppress his whimpering as Dean dabbed him with some alcohol.

"Fuck, fuck..." Sam groaned.

"Language, Sam," Dean scolded him. Typical brother.

After five painful minutes passed, Dean finished by putting bandaids on his cut. "There. So you want to tell me why you have been dressing up as _Mandy_ ," Dean purred at the name.

Sam snapped his head to him. He knew? He knew it was him all along. "Y-You knew?" Sam asked, dumbly. "Since when?" Dean never mentioned anything, or even hinted that it was Sam in disguise.

"Do I look like a dumbass?" Dean rolled his eyes. "I figured it out on our second date. It was so obvious, Sam. How Mandy would eat the same thing you would order? Rabbit food. Oh, and don't forget that both of you have the same colored eyes— Let's also not forget that you and Mandy were never together at the same time. Either you or her would make excuses to make sure I didn't notice it was you all along." He crossed his arms, but Dean didn't look pissed, only amused.

"If you knew all along... Why didn't you say anything?" Sam inquired, hurt. Was Dean playing with him all this time?

"Me?" he was offended, then said, "You're the one who made a fake persona! I was waiting until you had the courage to ask me. So I just played along."

Okay, Dean made a good point.

"You're not mad that I like you..." Sam whispered. "It's not normal—"

"So is hunting monsters and all that shit. Who gives a fuck? We haven't been normal since mom died in the fire," Dean countered. "Do you have any idea how long I've been in love with you? A long time." Dean had been in love with Sam for many years, when his feelings were mutual. He was overjoyed.

"You do?" Sam said in disbelief. It was like a dream come true.

"Yes, Sammy." Dean leaned dangerously close to his lips, "You've been mine since the day dad gave you to me." The words were whispered in a low tone between husky and seductive. "Am I yours?"

Sam nodded, vehemently. "Yes. Never want to let you got." He kissed Dean and put his arms around his neck. This was so much better than all the other kisses he had done with Dean. Sam wasn't pretending to be Mandy anymore, he was finally himself. Thereby, making it memorable. Sam bit Dean's lips— slowly pulling them— and he heard a moan coming from Dean.

"Fuck... Sam," Dean said between the kiss as he moved his lips to match with Sam's. Sam sometimes still couldn't believe that he was kissing Dean. It was as if he was dreaming— except he wasn't. The pain from his cheek definitely kept him awake. This was real.

Dean pulled away for a quick second and said, "Let's take this to the bedroom." Sam wasn't listening as he eagerly went back to kissing Dean, slithering his tongue inside his mouth. Dean closed his eyes and placed his hands on his waist.

He groaned in discomfort. Dean jerked away, scared that he did something Sam didn't like. But, when Sam rested his hand on his stomach and grimaced. Dean knew there was something else bothering him. Slowly, he peeled off Sam's sweater and removed the dress straps, Sam squirmed as Dean lowered half the dress down.

Dean's eyes widened, prompting Sam to blurt out, "It's not so bad." Fuck. He forgot about the punch he received there. Sam was too busy making out with Dean that it completely slipped his mind.

Sam's stomach was forming a dark purplish bruise like the size of a fist. Dean snarled, "Not so bad? Sam... Son of a bitch! If I knew who they were... I'd make sure they'd pay." He caressed his bruise.

"Make me forget, Dean. Make the hurting go away." That was all Dean needed to hear. He picked up his little brother, who wrapped his legs around his waist. They resumed back to kissing while Dean made his way to _their_ bed. Sam never once let go, even when he landed on the mattress.

Dean went lower, kissing his neck and nibbling his collarbone. Sam's head tilted back as he let a wanton moan out. "Dean..." His hands gripped Dean's hair, and his legs turned into jelly that he had no choice but to let go. Dean got closer between his legs, going lower and lower.

Sam's whole body felt like it was on fire and his heart wouldn't stop bouncing around his rib cage. He could feel his face getting hot and his cheeks must have been rosy red by now. He gazed at Dean with a hungry look— and whimpered— as Dean removed his shirt, revealing his toned torso.

"Hold on, baby boy. Going to make this the greatest experience for you." Dean pulled out a condom from his back pocket and lube was an easy access from the nightstand.

"Oh, aren't you romantic?" Sam's chuckle turned into mewls as Dean gripped his cock through his dress. "J-Jerk."

"Bitch," he said fondly. "Raise your hips up. I'd rather see you with no clothes on." Sam did as he was told, arching his back in order to lift his hips. Dean curled his fingers around the dress and pulled it down to his legs, displaying Sam's cock. "Commando, really?" he narrowed his eyes and an eyebrow rose in question.

"My boxers were too long! It was either commando or panties— Wipe that smirk off your face, Dean!" Sam blushed and turned his head to the side. "I prefer going commando." Seeing Dean with a Cheshire grin, made Sam feel queasy and funny... but in a good way.

"You're so cute." He tossed the piece of clothing on the floor. Now Sam was fully naked. Dean licked his lips as he took sight of every inch of Sam's body. Fuck. He was beautiful. Better than any girl Dean had ever seen. "And all _mine_."

"D-Dean," Sam stuttered, panting. He could feel his cock twitching in excitement as Dean kept eyeing him. "N-Need you." Dean took off his pants and briefs; both boys finally naked. Dean licked Sam's navel, while his fingers traced his soft skin, his muscles that were starting to grow from training. Sam's torso would be like Dean's in no time.

Dean was hard, his dick was throbbing and pulsing, he wanted to get inside Sam so bad. But he couldn't just yet. Dean would never forgive himself if he hurt Sam. He wanted to make it feel good for his first time. Curling his fingers around Sam's cock, he smirked when Sam moaned. Dean began to give a few strokes, secretly wanting to see Sam in a mess.

Sam's bottom lip trembled as Dean's tongue licked around his nipples. "You're messing with me," Sam forced back a moan, "Stop teasing and fuck me!"

Cocking his head up, Dean copied his words with a mocking smile. "Aren't you romantic— Ow!" Dean yelped when Sam pinched his nipple in annoyance. "Fucker." Dean attacked his mouth, both wrapping arms around each other and sharing laughter between the kisses. Dean ground their hips together. The pressure was incredible and breathtaking.

As he kept kissing Sam, Dean slid a slick finger inside his hole. Sam's eyes shut tightly and he gripped onto Dean's shoulders, accidentally digging his nails into his skin. Sam knew it would hurt— but damn... it felt like a slow burn.

"Want me to stop?" Dean frowned when he witnessed Sam's discomfort. "We don't have to do it now, Sam."

"It's fine. Keep going. Just feels weird," Sam muttered. "I know it gets better soon. I really want this with you."

"Have you been watching porn?" Dean teased, adding another finger. He made sure he coated his fingers with plenty of lube. Dean stretched Sam real good, making sure his fingers swirled around. God. He was so nervous. Dean was no virgin, but at the moment he was acting like a fucking beginner. His face was flushed and his chest kept moving up and down from breathing erratic.

"Shut up." Sam gritted his teeth, trying to think of something else beside the pain. Suddenly, the pain faded away as Sam arched his back and shouted, "Dean! Right there! Feels really good."

Dean pushed his fingers deeper into his pucker hole as hit the prostate every thrust. Sam wanted to come so badly, but wanted to wait until Dean was inside him. Cheesy? Yes. But Sam had been dreaming of this moment since forever.

Dean didn't waste any time. He pulled out his fingers and put the condom on. Sam spread his legs to make room for Dean. He had done some research about sex, Sam wasn't stupid, at least he hoped so. Dean's cock was huge, so Sam was definitely going to feel pain.

When his cock passed through his rim, Sam let out a groan and slightly whimpered. As soon as Dean was inside he didn't move, and said, "Whenever you're ready, baby boy." Dean kissed his tears away. When did Sam start to cry? He wasn't in tremendous pain but he was beyond nervous and scared. Who wouldn't be on their first time?

Every bone in his body was telling Dean to stop and pull out. Yet, if he did... Sam would think that he deserved someone better. And Dean didn't want to hear shit like that. Dean was going to show Sam that no one could compare and that he was the one for him.

A few minutes passed before Sam told him to move. Dean went slow and picked up his pace as Sam moaned. "This... feels good." Sam's mouth went slack as Dean pounded him. He wrapped his legs around Dean's waist so he could be closer to him. Every time Dean hit directly inside his prostate— Yes. He knew what that was— Sam's head hit back against the pillows as he came.

"Dean!"

Dean smiled softly when Sam said his name. It was music to his ears. Shit. Sam was so tight... and warm. Dean panted and thrust harder, his whole body stilled as he came deep inside Sam. Both boys were breathing heavily and letting the afterglow overtake them.

Sam's eyes were beginning to droop. He felt sleepy. Dean pulled out and threw the condom away, and lay right beside him. "We should really clean up... but looks like you're falling asleep." Sam barely caught the words, then he got on his side and hugged Dean.

"Sleep, Sammy." Dean whispered, pushing Sam's sweaty bangs away from his face.

Sam fell asleep, but before he did he felt Dean kiss his temple. Dean watched him sleep peacefully.

He still couldn't believe that Sam dressed up as _Mandy_ so he could spend time with Dean. Every time he had looked at his brother— with normal clothes— Dean would blush because Sam had no idea that he _knew_. Sam acted like Mandy didn't exist, and therefore, made Dean play along until Sam was ready to tell him the truth.

Dean snuggled close to Sam. Happy that he had his Sammy. Although, he wouldn't mind if Sam would wear Mandy's outfit once in a while. What could he say? Sam looked good in them.


End file.
